This proposal deseribes a program directed towards the total synthesis of aurodox (1) and application of the methodology to be developed to the synthesis of other natural and unnatural members of the elfamycin family. The proposed methodology includes (a) a stereocontrolled approach from carbohydrate precursors and (b) an asymmetric approach from achiral precursors designed also with high stereo control as a prime objective. Since aurodox (1) and its relatives exhibit potent antibiotic properties by inhibiting protein biosynthesis as well as ionophoric and growth-promoting activites, this program should contribute significantly to human and animal medicine as well as result in useful biological tools and new synthetic methodology.